Branching of poly(ADP-ribose): Synthesis of the Core Motif

The synthesis of the core motif of branched poly­(adenosine diphosphate ribose) (poly­(ADPr)) is described, and structural analysis reasserted the proposed stereochemistry for branching. For the synthesis, a ribose trisaccharide was first constructed with only α-O-glycosidic linkages. Finally, the a...

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Veröffentlicht in:Organic letters 2015-09, Vol.17 (17), p.4328-4331
Hauptverfasser: Kistemaker, Hans A. V, Overkleeft, Herman S, van der Marel, Gijsbert A, Filippov, Dmitri V
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Sprache:eng
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Zusammenfassung:The synthesis of the core motif of branched poly­(adenosine diphosphate ribose) (poly­(ADPr)) is described, and structural analysis reasserted the proposed stereochemistry for branching. For the synthesis, a ribose trisaccharide was first constructed with only α-O-glycosidic linkages. Finally, the adenine nucleobase was introduced via a Vorbrüggen-type glycosylation reaction. The orthogonality of the selected protecting groups was demonstrated, allowing for the construction of branched poly­(ADPr) oligomers in the near future.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02143